Toluene → 1-[6-[2-(4-Cyano-phenyl)-2H-pyrazol-3-yl]-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-3-piperidin-4-yl-urea

HRID 1497812Notes

Reaction equation

HRID 1497812 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([NH:17][C:18]2[N:50]=[C:21]3[C:22]([C:40]4[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:49])([F:48])[F:47])[CH:41]=4)=[C:23]([CH3:39])[C:24]([C:26]4[N:27]([C:31]5[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][CH:32]=5)[N:28]=[CH:29][CH:30]=4)=[CH:25][N:20]3[N:19]=2)=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C1(C)C=CC=CC=1>C(Cl)Cl>[C:37]([C:34]1[CH:33]=[CH:32][C:31]([N:27]2[C:26]([C:24]3[C:23]([CH3:39])=[C:22]([C:40]4[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:49])([F:47])[F:48])[CH:41]=4)[C:21]4[N:20]([N:19]=[C:18]([NH:17][C:15]([NH:14][CH:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)=[O:16])[N:50]=4)[CH:25]=3)=[CH:30][CH:29]=[N:28]2)=[CH:36][CH:35]=1)#[N:38]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 867081174-{3-[6-[2-(4-cyano-phenyl)-2H-pyrazol-3-yl]-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-ureido}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 730527101-[6-[2-(4-Cyano-phenyl)-2H-pyrazol-3-yl]-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-3-piperidin-4-yl-ureaYield 74.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{3-[6-[2-(4-cyano-phenyl)-2H-pyrazol-3-yl]-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-ureido}-piperidine-1-carboxylic acid tert-butyl ester (Int. 32, 95 mg, 0.14 mmol) in DCM (2 mL) was added TFA (1 mL) and the solution was stirred at RT for 1 hr, then toluene (10 mL) was added and the reaction mixture concentrated in vacuo. The reaction mixture was partitioned between DCM (15 ml) and aqueous 2 M Na2CO3, and the organic extract was dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a white solid (61 mg).

Workup

  1. concentrationthe reaction mixture concentrated in vacuo
  2. customThe reaction mixture was partitioned between DCM (15 ml) and aqueous 2 M Na2CO3
  3. extractionthe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0312a5c5b36e468b8c609d05fa134bc9
Source dataset
uspto-grants-2015_12
Patent number
US09199984B2

Reaction notes

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